Red basic dye.



STATES PATENT OFFICE,

' Wm KQNIG, 01' DRJA'SDER, GERMANY, ASSIGNOR- TO FARBEN'PABBIKEH vent.-1313133. BAYER & '00., OF ELBEBFELD, A CORPORATION OF GERMANY.

m nmc nn.

Io 1mm.

Specification oH-etto'n Potent.

, Application filed February 16, 1909. Serial Io. 478,288.

'n snocificstion.

In the application for Letters Patent Ser. H0. 465,102 it is stated thatdihydroindols, especially dihydroindol and its substitution products canserve as initial materials for the production of red to violet basiccoloring matters remarkable for their good fastto washing and to li tand their on treordinsry oleerness. I iave now found that dye-stuffs ofthe same valuable properties can be obtained b condensing thediligdroindois especially diliydroindol and it: so stitution productseither with aldebydes oi the following general formula:

aldehydes or oxixns or hydrazonee of the above given foriiml'e whereinmeans the residue of. dihydroindols. or their substitution productswith. secondary aromatic amins. I

The new products exist in two isomeric forms of different shades, e. g.according to the following formulae:

(or manning oryl; alk=aiky1 and X an acid Mi I i (a) Compounds of theformula 1.-In the Annalen der Ohem-ie, Vol. 338, 133, it is shown thatthe pyridin dyestufl's obtainable from secondary aromatic amine with anopen side-chain (e. g. monomethylanilin) split off one molecule of aminby treatment with alkslies, aldehydes of the formula:

- g n n being formed. These aldehydes can be easily condensed with onemolecule of dihyclroindols, especially dill droindol and itssubstitution roducts in t e presence of acids,red dyestuifs. ,eingobtained. The same products are obtained on using the oxims or hdrazones, semicarbazones, semioxamazones, nzhydrazids and aminoguanidinsof these aldehydes.

(6) Compounds of the formula 2.-Tltese compounds can be. obtained bycondensing with secondary aromatic amms the aldehydes of the formula:

(X, Y, Z=-hydrogen or any substitue'nts,

memin the residue of a dihydroindel.) These aidchydes-can be obtained bytreating the dyestuffs of' the earlier application Sen. No 465,102 withalkaliee. e-dyesmfl! of this kind have a yellows: shade than thosedescribed under a The new dyes are reddish products soluble in hot waterwith a reddish color, and d e in tanned cotton from yellow to red sh esorder to illustrate the new process more fully the following examplesere given, the parts being by weight:

Example 1: In a flask provided with a reflux condenser 1.87 parts of thealdehyde described in Annalen der Uhemie, Vol. 888, 127) of the formula:

2 parts of acetic acid er cent.) and 1.38. parts of dihydroslphemeylindol until the Patented Feb. 1, 1910; 7

' 'taining hydrochloric acid and common salt.

55. Stuff can be obtained by all wine; an secondary aromatic 21mins e.g. monomethy alcoholic solution of a mixture of 1 molecule mzilin,monuethylsnilic etc. may he use-xi. of the aldehyde nd 1 molecule of thehydro I Scarlet-red dyes are obtained from these lorid ofdihyciromeznethylindol to stand 2: amins. I r

for some time and then treating it as cle- Having new (la er-icedinvention and 60 scribed in the exm'nple. On using the main: in l :t erla ,periez'zned, of the aldehyde (M. P. 117} or the plienyL wh; 1 claimnew and desire to secure by hydrezonc (N. P. 141) the same dyestufi iLefiers Patent is:- is obtained :is described in Example 1. Sub-i l. Theherein-described new basic dyestitution nroducts of the aldehydegenerally f stuifs being derived from (1' iydroindois, 85 furnish bluerdyes. Thus (me can use a. g. i which ii are reddish cz vstalime productsthe aldehyde: soluble in hf: water with me color,

cm fiend dyeing tanned cmton from yellow to f red shades, substantiallyas ie .ibcd. f Q 2. The hercin;deecrit ed aw basic dye- 70 I /CH2 5 Hstufi' obtainable iron: the aldehyae x' -c H L V ,N-o=c( o=o 0 3 11/ \HH/ which can be obtained from the tetralnydroa 1 t 7 5 quinolin pyridio.dyestu (yellow prisms of and gee q- 1 111C191, l a he luster melting at113 or its 'fi 15 5 61 g .Qxim or hvdmzone ate e'ililfifl are soluble innot water with a mo Example e of the aldehyde i y o in who w a (3. R 1235); a: coloz and wh ch ayes tangled cotton & 30

{ clear scarlet shade, substantially as. (1-2; :H, f5; :cribcd. l g Intestimony whereof I have hereunto set }C 1'; H g I my can in thepresence of two subscribing witzzes es.

H/ \H 11 V W6 Y*' or 2.28 parts of its oxim (M. P. 181} which E l b naldehyde can be obtained by treatment with 'Witnesees:

alkaiies of the pyridin dyestufi obtainable HARRY A. 3163x203, fromdihydre-alpha-methylindol (see appl. Z PAUL 5am. i

. i "1? i i g. u. 1 l f I A The new dye separates in the she )e ofmicroscopic red needles which are fi tered of? L and dried. It is easilysoluble in alcohol g5 and in hot Water with a red color and dyes jtanned cotton a very clear scarlet shade fast to Washing and to light.The same dye- 2 Ser. No; -362) are heated on the water bath for severalhGdlS with 5 parts of alcohol, 1 part of acet c acid 60 per cent.) and1.33 parts of tetraliydrmguinolin. The mixture s then treated asclescrihegl under Example 1. The dye crystallizes in the shape ofmicroscopic needles of a green luster dyeing tanned cotton clearscarlet-red shades.

' Instead of tetrahydrsquinolii any other

